The Cincinnati Homeowner’s Fall Property Checklist: 30 Things to Do Before Winter

1. Keep Mowing While Your Grass Is Still Growing

Don't assume that September means mowing season is over.

Cool-season grasses can continue growing well into fall, depending on temperatures and weather conditions. Continue mowing as needed while your lawn is actively growing, and avoid letting the grass become excessively tall before winter.

The goal isn't to give your lawn one extremely short "final cut." Instead, maintain an appropriate mowing height throughout the remaining growing season.

2. Don't Let Leaves Build Up on the Lawn

One of the biggest fall maintenance jobs is managing leaves.

A thin layer of leaves may not seem like a problem, but allowing leaves to remain on the lawn for extended periods can block sunlight and air from reaching the grass underneath.

Instead of waiting until every tree has dropped its leaves, consider handling leaf cleanup in stages.

Regular fall leaf removal can make the final cleanup much easier and prevent your property from becoming overwhelmed when the leaves really start coming down.

3. Check Your Lawn for Bare or Thin Areas

Walk around your property and look for areas where the grass is thin, damaged, or completely bare.

Pay particular attention to:

• Areas under trees
• High-traffic areas
• Places where water collects
• Areas damaged by pets
• Slopes
• Areas affected by summer heat
• Places where grass struggled to grow

Fall can be an important time to address turf problems, but the right timing and approach depend on the grass type, soil conditions, weather, and the specific problem.

If you're unsure why an area of your lawn isn't growing properly, identify the cause before simply putting down more seed.

4. Look for Standing Water After Rain

This is one of the most important things to check before winter.

After a significant rainfall, walk around your property and look for areas where water remains long after the surrounding ground has drained.

Pay attention to:

• Muddy areas
• Standing water
• Erosion
• Washed-out soil
• Water flowing toward the house
• Water collecting near patios
• Saturated areas of the lawn
• Downspouts discharging too close to the foundation

A drainage problem that is easy to overlook during dry weather can become very obvious during a wet fall.

5. Inspect Your Downspouts

Your gutters can only do their job if the water has somewhere to go.

Check that downspouts are connected properly and that water is being directed away from areas where it can cause problems.

Look for soil erosion or concentrated water flow near the end of each downspout.

If you repeatedly notice water collecting in the same area, don't simply keep cleaning the gutter and assume the problem is solved. The issue may involve the way water is being moved across the property.

6. Check Your Gutters Before the Heavy Leaf Drop

Fall is one of the most important times to pay attention to your gutters.

Leaves, twigs, seeds and other debris can accumulate quickly once trees begin dropping their foliage.

Look for:

• Water overflowing during rain
• Sagging gutters
• Visible debris
• Downspouts that aren't draining
• Water running over the sides
• Staining on the exterior of the gutters

If you notice water overflowing during a storm, don't automatically assume you only need another cleaning. A blocked downspout, poor drainage, improper slope, or another issue could also be involved.

7. Don't Forget the Gutters After the Leaves Fall

Cleaning your gutters once in September doesn't necessarily mean you're finished for the season.

If your property has mature trees, additional leaves can accumulate throughout October and November.

A final late-fall inspection can be worthwhile, especially before freezing temperatures and winter precipitation arrive.

8. Inspect Areas Around Your Foundation

Walk around the outside of your home after a rainfall.

Look for places where water appears to be collecting against or very close to the foundation.

Also look for:

• Soil erosion
• Low spots
• Cracked or settled areas
• Water coming from downspouts
• Saturated soil
• Water flowing toward the house

The earlier you identify a recurring water problem, the more options you may have for addressing it.

9. Consider Whether You Have a Drainage Problem

Not every wet area requires a drainage system.

However, if the same location repeatedly collects water after rain, it is worth investigating why.

Depending on the property, drainage solutions can include changes to grading, extensions for downspouts, surface drainage, or systems such as French drains.

The right solution depends on where the water originates, where it needs to go, soil conditions, slope, and the layout of the property.

Don't install a drainage system simply because you saw one recommended online. Diagnose the water problem first.

10. Check Your Landscaping Beds

Fall is a great time to walk through your landscaping beds and identify areas that need attention.

Remove accumulated debris and leaves where appropriate, pull unwanted weeds, and look for damaged or struggling plants.

Also take note of areas where:

• Mulch has washed away
• Soil has eroded
• Water collects
• Plants have become overcrowded
• Edges have become difficult to maintain
• The landscape no longer matches the way you use the property

Taking pictures now can also help you remember what needs attention when planning future landscaping work.

11. Clean Up Leaves From More Than Just the Lawn

Leaves don't only accumulate on grass.

They can collect in:

• Landscaping beds
• Walkways
• Patios
• Driveways
• Around fences
• Under shrubs
• Around outdoor structures
• Near drains and drainage areas

Keeping leaves and debris under control throughout fall can make your property look better and make the final cleanup significantly easier.

12. Keep Leaves Away From Drainage Areas

This one is easy to overlook.

If your property already has drainage inlets, channels, or other areas designed to move water, make sure leaves and debris aren't blocking them.

A drainage system can't move water effectively if its intake or discharge area is obstructed.

After major leaf drops and heavy storms, take a quick walk around the property and check these areas.

13. Inspect Your Paver Patio and Walkways

Fall is also a good time to inspect hardscaping.

Look for:

• Settled pavers
• Uneven walking surfaces
• Gaps between pavers
• Weeds
• Poor drainage
• Areas where water collects
• Edges that have shifted

Small changes can become more noticeable after repeated cycles of rain, freezing temperatures, and thawing.

If you're considering a new patio, walkway, or paver project, fall is also a good time to start planning rather than waiting until you want the project completed immediately.

14. Look at Your Property From the Street

This sounds simple, but it can reveal things you don't notice when you're working in the yard.

Stand across the street and look at your property.

Ask yourself:

What looks overgrown?

Where are the leaves collecting?

Are the landscaping beds defined?

Does the patio or walkway look uneven?

Are there areas where water appears to be causing damage?

What would I want fixed before winter?

Taking a few minutes to look at your property as a visitor would can help you create a much better fall maintenance list.

15. Clean Exterior Windows Before Winter

Fall can be a good time to clean exterior windows and remove the buildup that accumulated throughout spring and summer.

Clean windows can also make a noticeable difference in how much natural light enters the home as the days become shorter.

If your property has difficult-to-reach windows, professional window cleaning can also eliminate the need to climb ladders or work from awkward locations.

16. Check Outdoor Areas Around Your Home

Walk around the entire exterior of your property instead of only checking the lawn.

Look at:

• Steps
• Walkways
• Patios
• Driveways
• Fences
• Retaining walls
• Landscaping
• Drainage areas
• Exterior lighting
• Outdoor structures

Fall is the perfect time to make a list of small problems before winter weather makes them harder to address.

17. Start Planning Your Holiday Lighting

If you want professional Christmas or Christmas Light Installation this year, don't wait until December to start thinking about it.

By September and October, homeowners can already begin deciding what type of display they want, where lights should go, and whether they want to use their own lights or have a professional installation designed for the property.

Think about:

• Rooflines
• Windows
• Trees
• Shrubs
• Entryways
• Walkways
• Garages
• Large architectural features

Planning early also gives you more time to make decisions instead of rushing immediately before the holidays.

18. Decide What Kind of Holiday Lighting You Want

There isn't one right option for every homeowner.

Some people want traditional seasonal lights installed and removed each year.

Others want a professionally designed display.

Some homeowners prefer permanent lighting that can be used throughout the year for different occasions.

Think about how you actually want to use your home before choosing the type of lighting installation.

19. Make Your Snow Removal Plan Before the First Snow

Snow removal is much easier to plan before the first storm than during one.

Think about:

• Driveways
• Sidewalks
• Steps
• Front entrances
• Mailboxes
• Parking areas
• Business entrances
• Areas that need to remain accessible

If you plan to hire a snow removal company, determine what areas need service and what level of service you expect before winter arrives.

20. Identify Slip and Fall Areas

Walk your property with winter in mind.

Are there areas that become especially slippery when wet?

Are there shaded walkways where ice could remain longer?

Are there steps that become difficult to access?

Are there low areas where water freezes?

Identifying these locations ahead of time can help you plan where snow removal and deicing attention may be most important.

21. Clean Up Before Winter Weather Makes It Difficult

Fall cleanup isn't only about making your property look good.

Leaves, branches and other debris can become more difficult to deal with once temperatures drop and the ground becomes wet or frozen.

Try to complete major cleanup projects before winter conditions make access more difficult.

22. Don't Ignore Small Drainage Problems

A small puddle may seem insignificant.

But if the same puddle appears every time it rains, it's telling you something about how water moves across your property.

Take pictures of recurring problem areas and pay attention to what happens during the next rainfall.

Where does the water start?

Where does it travel?

Where does it stop?

Does it move toward the house?

Does it disappear quickly or remain for hours?

Those observations can help identify the actual cause.

23. Take Before-and-After Photos

This is useful for homeowners planning future improvements.

Take pictures of:

• Landscaping beds
• Lawn problem areas
• Drainage issues
• Paver patios
• Walkways
• Gutters
• Exterior windows
• Areas needing cleanup

When spring arrives, you'll have a visual record of what you wanted to improve.

You can also use the photos to compare your property from year to year.

24. Make a Winter Problem List

Instead of trying to remember everything, write it down.

Create three categories:

Must Fix Before Winter

Problems involving water, unsafe walkways, drainage, gutters, or other issues that could become worse.

Would Like to Fix This Fall

Landscaping, cleanup, paver improvements, window cleaning, and other projects.

Plan for Spring

Larger landscaping projects, new patios, lawn renovations, planting projects, and other improvements that don't need immediate attention.

This simple system can keep your fall maintenance from becoming overwhelming.

25. Don't Try to Do Everything at Once

A common mistake is waiting until one weekend and trying to complete every fall task.

Instead, spread the work out.

For example:

September: inspect, plan and schedule.

October: manage leaves, clean up landscaping and address property problems.

November: complete final cleanup, inspect gutters and prepare for winter.

Before the first major snow: make sure drainage paths, walkways and entrances are ready.

The exact timing will vary with weather and the condition of your property.

26. Pay Attention to What the Rain Is Telling You

Rain exposes property problems that dry weather can hide.

During the next substantial rainfall, take five minutes to walk around—only where it is safe to do so—and observe your property.

Watch where water:

• Comes off the roof
• Leaves downspouts
• Crosses the lawn
• Collects
• Runs toward structures
• Erodes soil
• Pools near patios or walkways

This is one of the easiest ways to identify drainage issues before they become larger projects.

27. Think About Your Property as One System

Your lawn, landscaping, gutters, drainage, patios and walkways aren't completely separate.

Water from the roof enters the gutter system.

The gutters send water through the downspouts.

That water reaches the ground.

The grade of the property determines where it travels.

Landscaping, soil, hardscaping and drainage systems can all affect what happens next.

That's why solving the symptom isn't always enough.

If water keeps collecting in the same area, look at the entire path the water is taking.

28. Prepare Commercial Properties Too

Fall maintenance isn't only important for homeowners.

Businesses, rental properties, offices, churches, HOAs and other commercial properties also need to prepare for changing weather.

Commercial fall maintenance may include:

• Lawn maintenance
• Leaf cleanup
• Landscaping
• Gutter cleaning
• Window cleaning
• Drainage maintenance
• Holiday lighting
• Snow removal

Keeping these services organized before winter can make property maintenance much easier once weather conditions change.

29. Save This Checklist

Here's the short version you can screenshot:

September

☐ Inspect lawn condition
☐ Continue mowing as needed
☐ Identify bare or thin areas
☐ Check gutters
☐ Check downspouts
☐ Inspect drainage
☐ Look for standing water
☐ Check landscaping beds
☐ Inspect pavers and walkways
☐ Plan holiday lighting
☐ Start your winter maintenance list

October

☐ Keep leaves under control
☐ Clean landscaping beds
☐ Monitor drainage areas
☐ Clean exterior windows
☐ Address recurring water problems
☐ Inspect patios and walkways
☐ Schedule remaining fall projects
☐ Plan snow removal

November

☐ Complete major leaf cleanup
☐ Check gutters again after heavy leaf drop
☐ Clear drainage areas
☐ Finish important outdoor projects
☐ Prepare walkways and entrances
☐ Confirm winter service plans
☐ Complete final property inspection

Before Winter

☐ Gutters and downspouts functioning
☐ Drainage paths clear
☐ No obvious water pooling against the home
☐ Walkways inspected
☐ Snow removal plan established
☐ Landscaping cleaned up
☐ Outdoor problem areas documented